Preparation method of tralopyril

A molar ratio and equation technology, applied in the agricultural field, can solve the problems of low safety factor, many impurities, low yield, etc., and achieve the effect of less impurities, high purity and high safety factor

Pending Publication Date: 2022-01-04
山东亿嘉农化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of the above problems, the purpose of the present invention is to provide a preparation method of tresopride, which aims to solve the technical problems of many impurities, low purity, low yield and low safety factor in the synthesis process of tresopride in the prior art.

Method used

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  • Preparation method of tralopyril

Examples

Experimental program
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Effect test

Embodiment 1

[0028] The specific reaction process of the salt-forming reaction is described in detail in this example, and the alkali metal salt of p-chlorophenylaminoacrylonitrile can be successfully synthesized according to this synthesis method.

[0029] Put 112g of 1,1,1-trifluoroacetone (molecular weight 112.05) and 560mL of dichloroethane into a transparent reactor, transfer the reactor to a custom-made microwave oven and heat it to 60°C, and at the same time turn on a 300w quartz lamp or mercury lamp to irradiate the transparent Reactor, add bromine dropwise into the transparent reactor at a molar ratio of 1:1.06, under this condition, keep it for 5 hours, take a sample and control it, when the remaining 1,1,1-trifluoroacetone is ≤0.5%, the control is qualified . After the central control is qualified, add 168g of water, stir and wash for 0.5h, let stand to separate layers, separate the water layer, add 112mL dichloroethane to the water layer for extraction, combine the extract with...

Embodiment 2

[0031] The specific reaction process of the one-step bromination reaction is described in detail in this example, and 1-bromo-3,3,3-trifluoroacetone can be successfully synthesized according to this synthesis method.

[0032] Put 137.6g of p-chlorobenzonitrile crystals and 350mL of acetonitrile into the reactor, add potassium tert-butoxide at a molar ratio of 1:1.03, stir and raise the temperature to 70°C, and keep it warm for 7h. Filter out the resulting potassium salt through a funnel, and the filter cake is the potassium salt of p-chlorophenylaminoacrylonitrile, which is dried for later use.

[0033] The filtrate is a mixture of acetonitrile and by-product tert-butanol. After rectification, acetonitrile can be recycled.

Embodiment 3

[0035] The specific reaction process of the ring-forming reaction is described in detail in this embodiment. According to this synthetic method, 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile (pyrrole nitrile).

[0036] Add 216.7g of p-chlorophenylaminoacrylonitrile potassium salt, 650mL of cyclohexane and 5g of p-toluenesulfonic acid into the reactor, raise the temperature to 55°C, and add 1-bromo-3 , 3,3-Trifluoroacetone, after the dropwise addition is completed, keep warm at this temperature for 4 hours, take a sample for central control, and the remaining potassium salt ≤ 0.5% of the central control is qualified. After the central control is qualified, 250mL of water is added to the reactor, washed twice, and then separated into layers. The water layer is wastewater containing potassium bromide salt. The organic layer was distilled under normal pressure and reduced pressure to obtain a crude product, which was recrystallized by adding 350 mL of methanol,...

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Abstract

The invention discloses a preparation method of tralopyril, and particularly relates to the technical field of agriculture. The preparation method provided by the invention comprises the steps of 1, dissolving p-chlorobenzonitrile in acetonitrile, and carrying out a salt forming reaction under the catalysis of an organic base to obtain an alkali metal salt (I) of p-chlorophenyl amino acrylonitrile; 2, dissolving 1, 1, 1-trichloroacetone in alkyl chloride, carrying out a one-step bromination reaction with bromine, and carrying out extraction and distillation to obtain 1-bromo-3, 3, 3-trifluoroacetone (II); 3, dissolving the intermediate I in alkane, carrying out a ring closing reaction with the intermediate II through acid catalysis to obtain a 2-(4-chlorphenyl)-5-(trifluoromethyl)-1H-pyrrole-3-nitrile crude product, and carrying out distillation and recrystallization to obtain a pure product; and 4, performing two-step bromination on the intermediate III through bromine to obtain tralopyril. According to the intermediate obtained by the preparation method disclosed by the invention, the final product tralopyril is low in impurity content and high in product purity, the raw materials are simple and easy to obtain, the preparation process is simple, the reaction conditions are mild, and the preparation method is economical and environment-friendly and meets the requirements of industrial mass production.

Description

technical field [0001] The invention relates to the field of agricultural technology, in particular to a preparation method of treproride. Background technique [0002] Trilobide (bromopyrrolecarbil) is an important intermediate for the production of the low-toxicity and low-residue pesticide chlorfenapyr, and has a good development prospect. The current industrialized production routes all have problems such as more intermediate impurities, more hazardous waste products, limited product content and yield, and low safety factor. Contents of the invention [0003] In view of the above problems, the purpose of the present invention is to provide a preparation method of tresopride, aiming to solve the technical problems of many impurities, low purity, low yield and low safety factor in the synthesis process of tresopride in the prior art . [0004] In order to solve the above technical problems, the present invention provides the following technical solutions: [0005] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 王振江田辉张德元郭占师张晓娟
Owner 山东亿嘉农化有限公司
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